Trifluoroacetic acid → 1'-(Bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-one

HRID 251475

Reaction equation

HRID 251475 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:29])[NH:21]2)[CH2:17][CH2:16]1.[CH:30]12[CH2:36][CH:33]([CH:34]=[CH:35]1)[CH2:32][CH:31]2[CH:37]=O.C(O)(C(F)(F)F)=O>ClCCCl.CC#N.O>[CH:30]12[CH2:36][CH:33]([CH:34]=[CH:35]1)[CH2:32][CH:31]2[CH2:37][N:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:29])[NH:21]2)[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 15548169Spiro[isoindoline-1,4'-piperidin]-3-one

Product 1

HCID 580896271'-(Bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Sodium triacetoxyborohydride (31 mg, 0.15 mmol) was added to a stirred solution of spiro[isoindoline-1,4′-piperidin]-3-one 3a (20 mg, 0.10 mmol) and bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (18 mg, 0.15 mmol) in 1,2-dichloroethane (1 mL) and the mixture was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and the crude product was purified by preparative HPLC (5-70% CH3CN—H2O gradient with 0.05% TFA, 15 min) to give compound no. 267. LC/MS m/z [M+H]+ 309.0 retention time 1.7 min (10-90% CH3CN—H2O gradient, with 0.05% TFA, 5 min).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by preparative HPLC (5-70% CH3CN—H2O gradient with 0.05% TFA, 15 min)
  3. customto give compound no

Sources & evidence

ORD record
ord-8aef3106e8204065a3a9a129e087fa9a
Source dataset
uspto-grants-2011_01
Patent number
US07863449B2

Linked notes

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